Known for its parks, the two tallest buildings in the world, Prohibition history, its theater scene, Jazz, and more, Chicago has sights for all kinds of travelers. We've found several deals to help make a trip to Chi-town as affordable and enjoyable an excursion as possible.
Your Chicagoland vacation can't start until you're actually on your way there. So try for a cheap flight by searching the most recent AirTran sale, which offers 1-way fares for as low as $54. Or, if you're lucky enough to live near New York City, Spirit Airlines currently offers airfares between New York City and several US cities — particularly Chicago — starting at $9. If you don't mind a no-frills flight, it's easily one of the least expensive ways to get there. (Nope, walking doesn't count.)
Now that you have transportation to the Windy City (hopefully with a coat or three), you can choose from a variety of hotel packages. Of note is the pictured Congress Plaza Hotel (from $87 per night, a low by $12; scroll down to find it), with the welcome sight of Grant Park's greenery and views of Lake Michigan. Its doors open onto Michigan Avenue, a strip of the area's higher-end retail shops, Chicago's business district, and more. You can also check out the nearby Buckingham Fountain, get your exercise on at Lakefront Trail (which runs the length of Lake Shore Drive), or peruse the giant Harold Washington Library.
Another place to rest is the slightly smaller The Willows Hotel (from $48 per night, low by $27): Built during the "roaring 20s" Prohibition era, this hotel is a Historic Landmark, and it's located in Chicago's exclusive 1200-acre Lincoln Park area. Nearby, you can see the animals at the Lincoln Park Zoo or Conservatory, browse art pieces at Lillstreet Art Center, or even walk the sands of North Avenue Beach.
Made famous by the likes of Bob Fosse are Chi-town's theater and events scenes. We recommend checking out Fiddler on the Roof (for $30, 50% off), or head to the namesake The Chicago Theater for an event featuring comedians, music, radio shows, and more. If you've "been there, done that", you can go ultra alternative (and bring the kids) to the Noble Horse Theater's Nutcracker on Horseback ($10 for children, $15 for adults). It's a great example of the city's wide range of experiences.
If Chicago isn't currently on your radar, then be sure to check out our weekly roundup of the top travel deals from the past week for additional discounted flights, hotels, and vacation packages.
At the time of publication, these travel deals offered the lowest prices we could find. Deals may include blackout dates, additional taxes, and fees. Some of our prices are based on mandatory double occupancy.
Front page photo credit: Red State Blue State